My favorite views are from the mass ave bridge, seaport, and on top of the hills in Arlington
Yes, Quarry Hills is lovely with freshly fallen snow at sunrise, sunset or anytime. Enjoy a distant skyline view, plus have lunch in the restaurant.
BU bridge is a good view also, and of course the Longfellow Bridge looking to the Back Bay basin and the sailboats.
I like Storrow outbound at sunset around the Hatch Shell with sailboats dotting the Charles.
I've always enjoyed driving in from the Allston tolls and seeing the Charles and the entire skyline layed out before me...but drive too quickly, and it's gone.
The view from Paul Revere Park in the back of the Residence Inn in Charlestown toward TD Garden and the Zakim Bridge is nice. As is the area at that same hotel looking over the marina toward the Old North Church.
Love Flagship Wharf in Charlestown in back (or front) near the ferry. Nice view of TD Garden, Old North Church and the Custom House Tower, day or night. Saw the 2000 New Year's Eve midnight fireworks there.
I had a request to drive some photographers at midnight to Bunker Hill Monument and the gas lit streets around there for photos... as Boston as Beacon Hill in that little enclave.
The area in front of the Sonesta hotel in Cambridge is nice to sit on a bench at night. They reversed the driving direction years ago so not as easy to actually drive back there but can still be done, I think. Good view of the lighted Zakim bridge.
The North Point Park near Museum Way is nice to stroll and has a playground, plus it's fun to watch skateboarders at the new skateboard park not far, as is the newish park area around Nashua street.
I like Carson Beach late night though it's officially closed at dusk to cars in recent years. But I parked and walked for 30 minutes the other night...even saw someone on the beach on a blanket at midnight, on his back on his blanket, just enjoying his videos under the moonlight. But I think one can legally park at Castle Island for a stroll until 11 pm or so... loved my walk at sunset last year from there to Pleasure Bay onto Carson Beach for ice cream. Would've just kept walking to JFK library and Harbor Point and U-Mass Boston but was sore. I love that stroll near the water, looking toward Marina Bay, instead of just quickly driving as you enter the campus off Morrissey.
Marina Bay in Quincy: had a nice stroll around the boardwalk one summer evening last year. My little secret...Very nice with ice cream, bars, a couple of restaurants, great skyline view, water ferry at Squantum Point, nice new apartments...great views at sunset.
So yes, how can a driver be bored doing Uber and just drive around without sometimes taking a moment to enjoy some of his finds?